Hydrogen Peroxide → 2,3,4-Trimethoxyphenol

Participants

Reaction Steps

A solution of 2,3,4-trimethoxybenzaldehyde (1.00 g, 5.10 mmol) and 30 wt/v % hydrogen peroxide (0.672 mL, 6.52 mmol) in conc. H2SO4 (0.102 mL) and MeOH (10.19 mL) was stirred overnight at 25° C. under N2. After this time the mixture was diluted with water (20 mL) and extracted with CH2Cl2 (3×30 mL). The combined extracts were dried (MgSO4) and concentrated in vacuo to afford the crude product. This was purified by flash chromatography (Biotage Horizon, 40M, Si, ˜30 mL/min, 100% hexanes for 360 mL, gradient to 50% EtOAc in hexanes over 2088 mL) to afford 2,3,4-trimethoxyphenol, as a colorless oil. Rf=0.93 (50% EtOAc/hexanes). LCMS calc.=185.1; found=185.2 (M+H)+. 1H NMR (600 MHz, CDCl3): δ 6.62 (d, J=9.0 Hz, 1 H); 6.55 (d, J=8.9 Hz, 1 H); 5.49 (s, 1 H); 3.94 (s, 3 H); 3.89 (s, 3 H); 3.80 (s, 3 H).

Provenance & Evidence